BENNINGTON, VERMONT: PURE AMERICANA

With its independent bookstores, good-vibes cafe, and two craft brewers, downtown Bennington has all the trappings of a modern college town. A few minutes west on Main Street, past the old-timey Sunoco station run by Hemmings Motor News, the village of Old Bennington is pure Americana, right down to the big white church and Revolutionary War monument. In early fall, this 1761 town nestled between the Taconic and Green mountains might be the prettiest landscape in Vermont.

EN ROUTE

The wet summer could push foliage past late September, but definitely “get here before Columbus Day,” advise old-timers at the Bennington Station Saturday farmers market. “After that, we might get a frost, and all bets are off.” The Molly Stark Trail west from Brattleboro (Route 9) is a time-honored scenic drive. Hardwoods hug the roadsides, creating foliage bowers on the east and west ends. In between, the highlands open up for long views to distant peaks.

DON’T MISS

Dedicated in 1891, the 306-foot Bennington Battle Monument remains Vermont’s tallest structure. It commemorates the triumph over the British by General John Stark of the New Hampshire militia and Vermont’s Green Mountain Boys on August 16, 1777. Through October, take the elevator to the top for a bird’s-eye foliage view. The copper catamount statue on Monument Avenue marks the site of the tavern where the Colonials plotted strategy over pints. Nearby, the Old First Church (oldfirstchurchbenn.org) was dedicated in 1806 to house the congregation, organized in 1762. Contemporary signage recaps the poignant lives of some of the folks in the graveyard. Poet Robert Frost spoke for himself. His inscription reads “I had a lover’s quarrel with the world.” The Bennington Museum (benningtonmuseum.org) has the world’s largest public collection of paintings by folk artist Anna Mary Robertson Moses, a.k.a. Grandma Moses. Through November 5, a special exhibition juxtaposes her paintings with the sly primitivism of some modernist works.

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As a replacement for an 18th-century structure destroyed by fire in 1910, the Four Chimneys Inn (fourchimneys.com) is a relative newcomer in Old Bennington. The 11-acre estate has the grandeur of country homes from an earlier time. Americana continues to rule, even at mealtime. Set in a high-ceilinged former train station, Bennington Station restaurant (benningtonstation.net) is a good choice for dinner if you’re in the mood for classic American fine dining. By contrast, the 1940s Silk City streamline Blue Benn Diner offers both counter and booth seating, a wealth of American diner classics (including meat loaf and pot roast), and breakfast all day.

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Old First Church in Bennington, Vermont.

NORTH WOODSTOCK NEW HAMPSHIRE: MOUNTAIN HIGH

Long called “basecamp of the White Mountains,” North Woodstock smells like balsam fir — with just a whiff of boiling malt from a brewery. Peaks rise on the horizon in every direction, and the White Mountain National Forest blankets the countryside as far as the eye can see. For all its outdoors bona fides, this tiny village center is compelling in its own right. The brewpub, taverns, and sugarhouse are practically givens, but who would expect a Greek and a Chinese restaurant?

The speedy route from Boston is straight up I-93, taking Exit 32. You can better savor late September on the Kancamagus Highway (Route 112). Buy a parking pass at the Saco Ranger District visitors center, just a quarter of a mile from the east end of the highway, so you can stop to walk the piney path to Sabbaday Falls, a cataract tumbling into a sylvan grotto. Or just gorge on magnificent foliage by driving the legendary scenic route in one rush. The ribbon of asphalt and the flashes of acid-yellow and screaming-red leaves blend into a singular phantasmagorical experience.

Fadden’s General Store (nhmaplesyrup.com) has occupied the same building since 1896, and the Faddens have tapped the same maple grove since the 1930s, often winning the Carlisle Trophy for the state’s best syrup. The store corners the town’s market on camping, hunting, and fishing accessories, while other gift shops and an antiques marketplace satisfy the yen for recreational shopping. Full immersion in the White Mountains experience is the aim of Lost River Gorge and Boulder Caves (lostrivergorge.com). The mile-long boardwalk with more than 1,000 stairs follows a partially underground river through rugged caves. After going deep, go high with a gondola ride that takes you up to the summit of Loon Peak (loonmtn.com). The gondola runs through the Sunday after Columbus Day (October 15).

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The Woodstock Inn Station & Brewery (woodstockinnnh.com) complex is the biggest thing in town. The Main House is the hub, but the complex’s 40 rooms spill over into several other buildings. More than half of the 15 rooms in the Cascade Lodge sleep four or more. The Woodstock Station Restaurant has a huge menu of burgers, pizzas, and pubby comfort food. Out back, the Woodstock Inn Brewery offers daily tours. Their brews are on tap at the property’s several bars. At Peg’s Family Restaurant, the motto is “You’re never too early for lunch or late for breakfast.” The cash-only restaurant serves many dishes best topped with Fadden’s maple syrup, available on every table alongside the sugar and creamer.

Joe Klementovich

A section of New Hampshire’s Kancamagus Highway.

GREAT BARRINGTON, MASSACHUSETTS: STRAIGHT OUT OF CENTRAL CASTING

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Great Barrington would make a meaty subject for a sociology dissertation. The southern Berkshires town seems populated with equal parts Brooklyn hipsters, gentlemen farmers, and the offspring of Alice’s Restaurant-era hippies. All three mix easily in the downtown shops, which sell everything from avant-garde French and Italian eyewear to boho-chic consignment clothing to hand-forged gardening tools and dirt-scented candles. Located south of tweedier Lenox and Stockbridge, Great Barrington strikes an insouciant pose in the Berkshires, rather like a mountain biker who’s just crashed a garden party.

EN ROUTE

For the slow, scenic approach, take Exit 3 from the Massachusetts Turnpike to Route 20 west, one of the state’s oldest scenic highways. In Blandford, turn left onto Route 23 for an undulating drive past milk-and-egg farms, state forest land, and the Butternut ski area on Warner Mountain. The mixed hardwood forest along the road is thick with oaks and hickory that turn muted reds and golds starting in late September.

DON’T MISS

Great Barrington has shopping with personality, and browsing Main and Railroad streets can devour half a day, especially if you stop for a cafe au lait and a macaron at the local branch of Patisserie Lenox (patisserielenox.com). In spite of eBay’s domination of the once-ebullient collectibles industry, several small and interesting antiques shops still line Route 7. Dealers at Great Barrington Antiques Center (greatbarringtonantiquescenter.com) offer both fine traditional antiques and mid-century-modern goods. North of the village, give your wallet a break with a modest hike up Monument Mountain for sweeping views of the Housatonic Valley. Nearby Windy Hill Farm (windyhillfarminc.com) is well stocked with pumpkins and offers more than a dozen PYO apple varieties at any one time. For a taste of the region’s enduring folkie roots, catch the weekly Thursday night hootenanny at the Guthrie Center (guthriecenter.org) in Old Trinity Church, where the saga of Alice’s Restaurant began.

Zack Wittman

Railroad Street in Great Barrington.

EAT & SLEEP

Just south of the village, the Wainwright Inn (wainwrightinn.com) features big beds in big rooms (two with working fireplaces) and country Victorian decor. North of the village, across Route 7 from Monument Mountain, the Briarcliff Motel (thebriarcliffmotel.com) brings contemporary panache and high-thread-count sheets and plush-top beds to an updated 1960s motel that retains its ironic retro appeal. In the heart of “downtown” Great Barrington, the list of local farms and suppliers is almost as long as the rest of the menu at 20 Railroad Public House (20railroadpublichouse.com). Chef Sean Corcoran concocts a mean burger graced with house pickles.

windy hill farm

Windy Hill Farm in Great Barrington.

FRYEBURG, MAINE: NORTH COUNTRY FAIR

Most of the year, Fryeburg is a quiet place where the biggest ruckus downtown might be a lumber truck as it rumbles through or the baying of hunting dogs in the back of a pickup truck. In fact, that tranquillity has been the town’s summertime stock in trade since city folk started rusticating here in the late 19th century. But for eight days in October, the fairgrounds just north of downtown swell into one of the biggest villages in Maine. Harness racers, farmers, livestock breeders, and lumberjacks gather for one of the most enduring celebrations of farm and forest life in northern New England: the Fryeburg Fair.

EN ROUTE

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The prettiest route into Fryeburg follows the Pequawket Trail Scenic Byway (Route 113) north from its starting point at Route 25 in Standish. This landscape northwest of Portland navigates the foothills of the White Mountains west of Sebago Lake. From farm landscapes and second-growth woodlands around Baldwin and Hiram, the road opens up around Brownfield, with Burnt Meadow Mountain and the White Mountains on the northern horizon. Foliage starts early — trees are already turning — so there’s no time to waste.

DON’T MISS

Many Fryeburg visitors come to paddle the Saco River, once a site of major log drives. Through mid-October (except fair week), Saco River Canoe & Kayak (sacorivercanoe.com) rents gear and arranges pickups. Some folks like to paddle two or three days, enjoying primitive camping on the river’s sand beaches. For a long afternoon of stunning scarlet and yellow foliage, put in at Swans Falls across from the canoe rental. Pack a picnic and paddle slowly to soak it all in before being collected at Walker’s Bridge. From October 1 to October 8, everything revolves around the fair (fryeburgfair.org). Avoid the big weekend crowds by attending earlier in the week for the skillet and anvil throws, the woodsmen’s competitions, and the animal judging. You can still catch harness racing, country singers onstage, and the razzmatazz of the midway.

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Many fairgoers camp at one of the 3,000 sites at the fairground. North of town, the Old Saco Inn (oldsacoinn.com) offers its guests complimentary canoes and kayaks for plying the Old Saco River — a meandering waterway snipped from the river’s main course by an early 1800s canal. Down a dirt road, the contemporary inn and carriage house sit on a riverside mountain meadow. Enjoy polished contemporary American dinners at the downtown Oxford House Inn (oxfordhouseinn.com), where the all-season back porch has outstanding views of the White Mountains.

The Fryeburg Fair.

OLD LYME, CONNECTICUT: PICTURE PERFECT

It’s hard to know where to look first in Old Lyme — at the riotous flower gardens, the titanium-white Congregational church, or the dappled autumn light falling on the 17th-century town green. Starting around 1900, American Impressionist painters descended on the small community for an annual months-long plein-air paint-a-thon. A century later, Old Lyme’s historic district remains a genteel preserve of American Impressionism. Have a look — easels optional.

EN ROUTE

The deep woods lining I-395 from the Massachusetts Turnpike south to the Connecticut shore blaze with color in mid-October. Follow Route 156 from Niantic for a rolling country drive just out of sight of Long Island Sound. McCurdy Road connects to the village at the Old Lyme Green and the unmistakable First Congregational Church. From here, most of the essential sights line a 1-mile stretch of Lyme Street.

DON’T MISS

Readjust how you see the world by spending a few hours at the Florence Griswold Museum (florencegriswoldmuseum.org). For more than three decades, the painters of what became the Lyme Art Colony spent collegial summers at Griswold’s sea captain’s manse-turned-boardinghouse. They left their marks — quite literally — on the walls and doors. They often found inspiration in the gardens and along the backyard bank of the Lieutenant River. The New England Landscape Invitational fills three of the four skylit galleries at the nearby Lyme Art Association through November 3. A two-minute walk from the Old Lyme Green, the Cooley Gallery (cooleygallery.com) sells work from Lyme artists, including many early American Impressionists. Sculptor Gilbert V. Boro sees landscape differently — as a setting for his giant abstract sculptures. At Studio 80 + Sculpture Grounds (sculpturegrounds.com), you can contemplate his work and enjoy other pieces by invited artists.

EAT & SLEEP (& CATCH SOME TUNES)

In the 1930s, widow Henrietta Greenleaf Lindsay transformed her sprawling Colonial home into the Bee & Thistle Inn (beeandthistleinn.com), featuring 10 genteel guest rooms. Those looking for a true escape might try the Old Lyme Inn (oldlymeinn.com), where local Impressionist canvases from the early 20th century set the tone and where five of 13 rooms are TV-free. The other eight rooms feature gas fireplaces along with televisions. The Old Lyme Ice Cream Shoppe (oldlymeicecreamshoppe.com) serves soup, salads, and sandwiches at lunch. Save room for a scoop of seasonal pumpkin ice cream studded with caramel and glazed nuts. The Old Lyme Inn also serves contemporary American fare at lunch, dinner, and Sunday brunch. It offers jazz on Friday and Saturday nights at the Side Door jazz club (thesidedoorjazz.com). For roots music, check out the retro coffeehouse vibe at Nightingale’s Acoustic Cafe (musicnowfoundation.org).

veronica grech

BRISTOL, RHODE ISLAND: GORGEOUS LATE BLOOMER

Its weather tempered on two sides by Narragansett and Mount Hope bays, Bristol enjoys a languorous fall. Foliage often peaks as late as the third week of October, and the lush gardens and verdant landscapes outlast much of New England. The former shipping harbor now bristles with the masts of daysailers and the antennae of sport vessels. Walk uphill from the water through the compact village center of boutiques, restaurants, and gaggle of real estate offices. Gentlemen of leisure carry on the tradition of the Loafers’ Corner at State and Hope streets. Perched on public benches and their own folding chairs, they solve the town’s problems first — then the world’s.

EN ROUTE

Day-trippers can pedal into town on the East Bay Bike Path, which starts at India Point Park in Providence. The 14.5-mile bikeway, largely following a rail bed, tunnels through woods and skirts marshes along Narragansett Bay’s eastern shore. Drivers on Route 114 enjoy the same coastal plain, bright with foliage and broad ocean light. Enter Colt State Park through a corridor of maple trees. The vast green lawns provide sweeping views of the bay. Adjacent to the park, the 1790s salt-marsh farm, Coggeshall Farm Museum (coggeshallfarm.org), bustles with activity on harvest weekends. In late October a new gallery opens, filled with fascinating farm implements.

DON’T MISS

Gracious Colonial and Federal homes line Hope Street. But the domestic queen of Bristol is Blithewold (blithewold.org). Tours of the country mansion end Columbus Day, but the 33 acres of artful landscape and exuberant gardens remain open. Blooms peak in October, as late dahlias bow their gaudy heads. East of town, Mount Hope Farm (mounthopefarm.org), ancestral home of Wampanoag leader Metacom, sprawls above Mount Hope Bay. Its Farmfest celebration is October 28, but the year-round Saturday morning farmers market draws many regional growers. Walking trails include a mile-long path from the 18th-century farmhouse to a rustic cabin on the shore.

EAT & SLEEP

Make the Bristol Harbor Inn (bristolharborinn.com) your waterfront base. Recently refreshed, the posh 44-room boutique hotel sits on the circa-1800 site of a rum distillery. It never hurts to ask for one of the four king end rooms with harbor views. For breakfast and lunch, it’s hard to beat the Beehive Cafe (thebeehivecafe.com), where a chalkboard lists the local farms providing food on that day’s menu. For Rhode Island seafood such as clam cakes or cod baked in tomato sauce, try Quito’s (quitosrestaurant.com) on the harbor. The outdoor patio beckons on a warm day.